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6-Mercaptopurine

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Name

6-Mercaptopurine

EINECS 200-037-4
CAS No. 50-44-2 Density 1.82 g/cm3
PSA 89.45000 LogP 1.01550
Solubility 124mg/L(25 oC) Melting Point 241-244 °C
Formula C5H4N4S Boiling Point 471.018 °C at 760 mmHg
Molecular Weight 152.18 Flash Point 238.663 °C
Transport Information N/A Appearance yellowish-greenish solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 50-44-2 (6-Mercaptopurine) Hazard Symbols N/A
Synonyms

6-Mercaptopurinum;6-Mercaptopurine, >99%;NSC-755;Mercaleukin;Purine-6-thiol, monohydrate;6-mercapto-;9H-Purin-6-yl hydrosulfide;6-Thioxopurine;U-4748;Puri-Nethol;1,7-Dihydro-6H-purine-6-thione;6-Thiopurine;6H-Purine-6-thione, 1,7-dihydro-;7-Mercapto-1,3,4,6-tetrazaindene;Hypoxanthine, thio-;6-Purinethiol;Mercaleukim;7H-purine-6-thiol;

Article Data 21

6-Mercaptopurine Synthetic route

2562-52-9

2,6,8-trichloro-7H-purine

50-44-2

6H-purine-6-thione

Conditions
ConditionsYield
With potassium hydrosulfide und Erwaermen des Reaktionsprodukts mit einem Gemisch von Jod, konz.HI und rotem Phosphor;
2846-90-4

[1,3]thiazolo[5,4-d]pyrimidin-7-amine

50-44-2

6H-purine-6-thione

Conditions
ConditionsYield
at 190℃;
at 190℃;
64194-58-7

6-amino-5-formylamino-3H-pyrimidin-4-one

50-44-2

6H-purine-6-thione

Conditions
ConditionsYield
With pyridine; tetraphosphorus decasulfide
With tetraphosphorus decasulfide; tetralin
500542-05-2

N-(4-amino-6-thioxo-1,6-dihydro-pyrimidin-5-yl)-formamide

50-44-2

6H-purine-6-thione

Conditions
ConditionsYield
With formamide at 200℃;
20271-18-5

5-Aminoimidazole-4-thioamide

50-44-2

6H-purine-6-thione

Conditions
ConditionsYield
at 200℃;
87-42-3

6-chloro-7H-purine

17356-08-0

thiourea

50-44-2

6H-purine-6-thione

Conditions
ConditionsYield
With ethanol
68-94-0

1,7-dihydro-6H-purin-6-one

50-44-2

6H-purine-6-thione

Conditions
ConditionsYield
With tetraphosphorus decasulfide; tetralin
With pyridine; tetraphosphorus decasulfide
Multi-step reaction with 2 steps
1: N,N-dimethyl-aniline; POCl3
2: ethanol
View Scheme
126616-94-2

S6-(N-methyl-N-methoxycarbonyl)aminomethyl-6-mercaptopurine

50-44-2

6H-purine-6-thione

Conditions
ConditionsYield
With phosphate buffer; water at 32℃; Rate constant; Mechanism; pH 7.1;
126646-36-4

S6-(N-methyl-N-ethoxycarbonyl)aminomethyl-6-mercaptopurine

50-44-2

6H-purine-6-thione

Conditions
ConditionsYield
With phosphate buffer; water at 32℃; Rate constant; pH 7.1;
126616-96-4

S6-(N-ethyl-N-methoxycarbonyl)aminomethyl-6-mercaptopurine

50-44-2

6H-purine-6-thione

Conditions
ConditionsYield
With phosphate buffer; water at 32℃; Rate constant; pH 7.1;

6-Mercaptopurine Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 240.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 26 ,1981,p. 249.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 26 ,1981,p. 249.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Studies (ipr); Equivocal Evidence: rat CANCAR    Cancer. 40 (1977),1935. ; (ipr); Clear Evidence: mouse CANCAR    Cancer. 40 (1977),1935. . EPA Genetic Toxicology Program.

6-Mercaptopurine Specification

6-Mercaptopurine, with the CAS NO.50-44-2, is an immunosuppressive drug. It has the Synonyms of LEUKERIN; 1,7-Dihydro-6H-purine-6-thione; 7H-PURINE-6-THIOL; 7-mercapto-1,3,4,6-tetrazaindene; 6-MERCAPTOPURINE; 6-PURINETHIOL; 6-THIOPURINE; 6-thioxopurine. It is used to treat leukemia, pediatric non-Hodgkin's lymphoma,[citation needed] polycythemia vera, psoriatic arthritis, and inflammatory bowel disease. 6-Mercaptopurine can be obtained by the reaction of seq xanthine with phosphorus pentasulfide.

Physical properties about 6-Mercaptopurine are: (1)ACD/LogP: -0.632; (2)ACD/LogD (pH 5.5): -0.64; (3)ACD/LogD (pH 7.4): -0.82; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 10.71; (7)ACD/KOC (pH 7.4): 6.95; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)Index of Refraction:1.941; (11)Molar Refractivity: 40.028 cm3; (12)Molar Volume: 83.36 cm3; (13)Polarizability:15.868 10-24cm3; (14)Surface Tension: 75.4020004272461 dyne/cm; (15)Density: 1.826 g/cm3; (16)Flash Point: 255.372 °C; (17)Enthalpy of Vaporization: 76.687 kJ/mol; (18)Boiling Point: 498.646 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10);
(2)InChIKey=GLVAUDGFNGKCSF-UHFFFAOYSA-N;
(3)Smilesc12c(nc[nH]c1=S)nc[nH]2

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
hamster LD50 intraperitoneal 364mg/kg (364mg/kg)   Archives of Toxicology. Vol. 32, Pg. 1, 1974.
man TDLo oral 40mg/kg/1W-I (40mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Archives of Dermatology. Vol. 122, Pg. 1413, 1986.
mouse LD50 intraperitoneal 80mg/kg (80mg/kg)   Cancer Research. Vol. 42, Pg. 122, 1982.
mouse LD50 intravenous 80mg/kg (80mg/kg)   Cancer Research. Vol. 42, Pg. 122, 1982.
mouse LD50 oral 260mg/kg (260mg/kg)   Cesko-Slovenska Farmacie. Vol. 14, Pg. 389, 1965.
mouse LD50 subcutaneous 100mg/kg (100mg/kg) IMMUNOLOGICAL INCLUDING ALLERGIC: DECREASE IN HUMORAL IMMUNE RESPONSE Journal of Medicinal Chemistry. Vol. 18, Pg. 320, 1975.
rat LD50 intraperitoneal 159mg/kg (159mg/kg)   Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 41, Pg. 571, 1984.
rat LD50 intravenous 250mg/kg (250mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1467, 1970.
rat LD50 oral 277mg/kg (277mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 15, Pg. 1037, 1973.
rat LD50 parenteral 250mg/kg (250mg/kg)   Recent Results in Cancer Research. Vol. 52, Pg. 76, 1975.
rat LD50 subcutaneous 90mg/kg (90mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 15, Pg. 1037, 1973.

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